US7186814B2 - Bioconjugate-nanoparticle probes - Google Patents
Bioconjugate-nanoparticle probes Download PDFInfo
- Publication number
- US7186814B2 US7186814B2 US10/291,291 US29129102A US7186814B2 US 7186814 B2 US7186814 B2 US 7186814B2 US 29129102 A US29129102 A US 29129102A US 7186814 B2 US7186814 B2 US 7186814B2
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- nanoparticle
- bioconjugate
- oligonucleotide
- probes
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- 0 *CCS Chemical compound *CCS 0.000 description 15
- WHOGPYOPKUAQGX-OGYDOGDXSA-N CC/N=C/OP(C)OC1C[C@H](N2C=NC3=C2N=C(F)N=C3OCCC2=CC=C([N+](=O)[O-])C=C2)O[C@@H]1CC.CN1C=NC2=C1N=C(F)N=C2OCCC1=CC=C([N+](=O)[O-])C=C1 Chemical compound CC/N=C/OP(C)OC1C[C@H](N2C=NC3=C2N=C(F)N=C3OCCC2=CC=C([N+](=O)[O-])C=C2)O[C@@H]1CC.CN1C=NC2=C1N=C(F)N=C2OCCC1=CC=C([N+](=O)[O-])C=C1 WHOGPYOPKUAQGX-OGYDOGDXSA-N 0.000 description 1
- KDWKWRNZODKJLC-UHFFFAOYSA-N CC12CCC(O)CC1CCC1C2CCC2(C)C1CCC21OC2CSSCC2O1 Chemical compound CC12CCC(O)CC1CCC1C2CCC2(C)C1CCC21OC2CSSCC2O1 KDWKWRNZODKJLC-UHFFFAOYSA-N 0.000 description 1
- LXXQSRLLYFWKBA-CXWHKCQTSA-N [2H]C([3H])OCC1OC(N2C=C(CCSSC(C)(C)C)C(=O)NC2=O)CC1OP(C)OCC[N+]#[C-] Chemical compound [2H]C([3H])OCC1OC(N2C=C(CCSSC(C)(C)C)C(=O)NC2=O)CC1OP(C)OCC[N+]#[C-] LXXQSRLLYFWKBA-CXWHKCQTSA-N 0.000 description 1
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Classifications
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
- G01N33/585—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances with a particulate label, e.g. coloured latex
- G01N33/587—Nanoparticles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/543—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals
- G01N33/54306—Solid-phase reaction mechanisms
Abstract
Description
wherein n, m, X, Z and Q are as defined above for bioconjugate (A), and each L is a linker formed by the coupling of two moieties selected from the group consisting of COOH, NH2, CHO, Cl, Br, I, NCO, NCS, allyl, and CH3CO2 −, or L is —C(═NH2Cl)(CH2)3 −. The bioconjugate is coupled to the nanoparticle through the sulfur groups (—SH).
wherein n, m, X, Z and Q are as defined above for bioconjugate (A), and R is an organic moiety such as an alkyl group such linear or branched C1–C8 alkyl, and wherein the bioconjugate is coupled to the nanoparticle through the disulfide groups (—S—S—).
wherein n, m, X, Z, L and Q are as defined above for bioconjugate (B), and wherein W is an aliphatic or aromatic group. The bioconjugate is coupled to the nanoparticle through the sulfur groups (—SH and S—S).
wherein n, m, X, Z and Q are as defined above for bioconjugate (A), and wherein W is an aliphatic or aromatic group. The bioconjugate is coupled to the nanoparticle through the sulfur groups (—SH and S—S).
wherein n, m, X, Z, L and Q are as defined above for bioconjugate (B), and wherein the bioconjugate is coupled to the nanoparticle through the sulfur groups.
wherein n, m, X, Z, L, W, R and Q are as defined above. The bioconjugate is coupled to the nanoparticle through the sulfur groups.
v is 0–30 and R1 is H or is G(CH2)v, wherein G is —CH3, —CHCH3, —COOH, —CO2(CH2)vCH3, —OH, or —CH2OH.
Protocol. 1. Incorporate 2-F-dI at the desired position using standard synthesis conditions with 2-F-dl-CE phosphoramidite (commercially available form Glen Research). 2. Nucleoside Conversion: At the conclusion of oligonucleotide synthesis, rinse the synthesis column with acetonitrile and roughly dry the support with argon. Dissolve desired primary amine in 1–2 mL DMSO (other organic solvent can be substituted depending on solubility of amine) at a concentration of 0.5 M. Treat the support in the column with the amine solution using two 1 mL disposable syringes. Incubate for 18–24 hours at RT to effect conversion. An alternate approach is to transfer the support to a Sarstedt tube, add the amine solution and incubate as above. 3. Preliminary O6 Deprotection: Wash the
Claims (25)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/291,291 US7186814B2 (en) | 2001-11-09 | 2002-11-08 | Bioconjugate-nanoparticle probes |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US34823901P | 2001-11-09 | 2001-11-09 | |
US10/291,291 US7186814B2 (en) | 2001-11-09 | 2002-11-08 | Bioconjugate-nanoparticle probes |
Publications (2)
Publication Number | Publication Date |
---|---|
US20030143598A1 US20030143598A1 (en) | 2003-07-31 |
US7186814B2 true US7186814B2 (en) | 2007-03-06 |
Family
ID=28454565
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/291,291 Active - Reinstated 2024-06-09 US7186814B2 (en) | 2001-11-09 | 2002-11-08 | Bioconjugate-nanoparticle probes |
Country Status (8)
Country | Link |
---|---|
US (1) | US7186814B2 (en) |
EP (1) | EP1466015B1 (en) |
JP (1) | JP4220397B2 (en) |
AT (1) | ATE403751T1 (en) |
AU (1) | AU2002367817B2 (en) |
CA (1) | CA2466656C (en) |
DE (1) | DE60228128D1 (en) |
WO (1) | WO2003081202A2 (en) |
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CA2466656A1 (en) | 2003-10-02 |
AU2002367817B2 (en) | 2008-05-29 |
US20030143598A1 (en) | 2003-07-31 |
ATE403751T1 (en) | 2008-08-15 |
CA2466656C (en) | 2013-07-02 |
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WO2003081202A3 (en) | 2004-07-22 |
EP1466015B1 (en) | 2008-08-06 |
JP4220397B2 (en) | 2009-02-04 |
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JP2005519627A (en) | 2005-07-07 |
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